Jack White Tells Bob Dylan Why He Was So “Jealous” of Artists Like Him: “You Guys Had It So Lucky”

Of the few certainties of life, one is undoubtedly different generations’ susceptibility to falling into the “grass is greener” mindset when looking at their younger or older counterparts. An outside perspective will always be askew from what the insiders’ perspective looks like, and this is no less true for musicians. Jack White shared his thoughts on the matter in a 2018 interview with Dan Rather, revealing why he thought musicians of the 1960s had it so much easier than artists of the 2020s.

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White told Rather about a time he admitted to Bob Dylan that he was “jealous” of him. But White wasn’t jealous of Dylan’s personal accolades or catalogue. Dylan was one of countless musicians White envied for getting to cut their teeth in the 1960s. White told Dylan, “You know, in a lot of ways, you guys had it so lucky in the sixties.”

The White Stripes founder began listing all of the things that contributed to the experimentation, style, and voice of the 60s. “All these recording techniques had never been tried before,” White explained. “No one had ever tried it. The Civil Rights Movement was coming to a head. You had that to sing about. Vietnam War. The whole world was changing. There was so much to sing about. It’s like shooting fish in a barrel to sing about those kind of songs right now.”

Jack White Had a Point About Bob Dylan and Others, but It’s a Delicate Balance

That the 1960s were full of songwriting material and musical innovation is undeniable, although one would have to ignore a lot of realities to truly believe the tumultuousness of the Vietnam War or the Civil Rights Movement was “lucky.” From a musical perspective, Jack White certainly made a point about the advantages of 60s musicians. However, an argument leaning too far in this direction is ripe for a curmudgeony perspective, which White admittedly flirts with.

Although he does so gingerly, White calls the younger generations “entitled,” saying he doesn’t “see beauty” in teenagers “sitting next to each other, texting.” This writer humbly suggests that this is the same old-man rant, reheated, about not understanding how younger generations connect with each other. Moreover, changes in recording technology and online accessibility might have downsides. But it’s significantly easier to get started in music now than it was in the 60s.

Still, in some ways, White was right on the money about making music in the 1960s versus making music in the 2020s. And if anyone would know about this particular argument, it would be him. Jack White, Nashvillian of many musical projects and artistic endeavors, is no stranger to the idea of diversifying his business strategy.

Speaking to Dan Rather, White said this is more out of necessity than preference. “I am a little bit jealous of the artists from the other decades because it seemed like you could just do your job and not have to worry about this periphery of stuff. In a lot of ways, Third Man Records is a reflection of the present. The idea that I have to sort of be a hustler now to just be a musician. You have to sell yourself all the time.”

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